1. Field of the Invention
This invention relates to aminocyclitols having stereospecific structure and optical activity and further to a process for their production. The above compounds are suitable particularly for use as starting materials in the preparation of medicinal products such as antibiotics and anticarcinogens and of agricultural chemicals.
2. Description of the Prior Art
Aminocyclitols, also termed aminosaccharides, are compounds obtained by rearranging a cyclic alcohol to have amino groups substituted for the hydroxyl groups. These compounds have gained a high reputation since streptamine, one member of the aminocyclitol family, was discovered to be a key component for streptomycin. Several other members of this family are currently applicable to certain antibiotics. Furthermore, the aminocyclitol compounds serve to construct glycoconjugates which occur naturally widely as polysaccharides and have a biologically important role to maintain the life of animals.
Aminocyclitols, from the standpoint of their unique significant function, have been synthesized with various chemical modes of reaction. One such mode is disclosed by S. Ogawa et al., Chem. Lett., 1518 (1985) in which an aminosaccharide is prepared by reacting furan with acrylic acid through the Diels-Alder procedure, thereby forming 1,4-anhydrocyclohexane, and subsequently by decomposing the same with acetic acid to open the anhydro ring, followed by azidation, reduction and other necessary treatments. It is known from H. Paulsen et al., Liebigs Ann. Chem., 2180-2203 (1981) that valienamine of optical activity can be derived via 21 steps of reaction from L-quebrachitol of natural origin. Benzene glycol is employed as a starting material in an aminocyclitol synthesis of M. Nakajima et al., Liebig Ann. Chem., 689, 243 (1965). A disulfonate or cis-1,4-diepoxide derivative of an inositol is reacted with hydrazine as reported by F. W. Lichtenthaler, "Newer Methods of Preparative Organic Chemistry", IV, 155 (1968) and by S. Ogawa, J. Syn. Org. Chem., Japan, 27, 731 (1969).
The foregoing aminocyclitol syntheses of the prior art, however, have a drawback in that they involve numerous complicated reaction steps including in most cases a tedious optical resolution step and entail low product yield.